Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis. Unusual Truce-Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone
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Kimbaris, A.
Cobb, J.
Tsakonas, G.
Varvounis, G.
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Elsevier
Abstract
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peer reviewed
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Tetrahedron
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Reaction of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfonyl} acetone with sodium hydroxide with or without zinc gave 1-(2-nitrophenyl)(1H-pyrrol-2-ylsulfonyl)methane by a Truce-Smiles type of transformation and 1-(2-nitrophenyl)-2-methylsulfonylpyrrole by deacetylation. Similar treatment of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfinyl}acetone gave only 1-(2-nitro-phenyl)(1H-pyrrol-2-ylsulfinyl)methane. 1-{[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetone, 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}-1-phenylethan-1-one or 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetonitrile were reductively cyclised with sodium borohydride and 5% palladium-on-carbon into 6-methyl(or phenyl)-5,6-dihydro-7H-pyrrolo[1,2-a][3.1.6]benzothiadiazocin-7-ol or 6-amino-5H-pyrrolo[1,2-a][3.1.6]benzothiadiazocine-7-oxide, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
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Keywords
pyrroles, pyrrolobenzothiadiazocines, cyclisation, reduction, truce-smiles rearrangement, reverse-transcriptase inhibitors, pyrrolyl aryl sulfones, heterocyclic-systems, 5,5-dioxide, derivatives
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<Go to ISI>://000223935100005
http://ac.els-cdn.com/S0040402004011597/1-s2.0-S0040402004011597-main.pdf?_tid=d14247a2-34ac-11e3-b43e-00000aab0f27&acdnat=1381740440_c92b877b397b84078e419318666ebed4
http://ac.els-cdn.com/S0040402004011597/1-s2.0-S0040402004011597-main.pdf?_tid=d14247a2-34ac-11e3-b43e-00000aab0f27&acdnat=1381740440_c92b877b397b84078e419318666ebed4
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en
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας